Potassium Carbonate → (S)-tert-Butyl 2-(2-(2-chloro-5-fluoropyrimidin-4-ylamino)-3,3-dimethyl-butylthio)ethanoate

HRID 1055129노트

반응식

HRID 1055129 반응식
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@@H:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:10][SH:11])[C:5]([F:16])=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]>CC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@@H:9]([C:12]([CH3:13])([CH3:15])[CH3:14])[CH2:10][S:11][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:5]([F:16])=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 86714752(S)-2-(2-chloro-5-fluoropyrimidin-4-ylamino)-3,3-dimethylbutane-1-thiol2회

생성물 1

HCID 86714775(S)-tert-Butyl 2-(2-(2-chloro-5-fluoropyrimidin-4-ylamino)-3,3-dimethyl-butylthio)ethanoate

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a stirring suspension of (S)-2-((2-chloro-5-fluoropyrimidin-4-yl)amino)-3,3-dimethylbutane-1-thiol, 77a, (1.50 g, 5.69 mmol) and K2CO3 (2.36 g, 17.06 mmol) in acetone (15 mL) was added tert-butyl bromoacetate (1.26 mL, 8.53 mmol). The suspension was stirred at room temperature for 18 hours. The resulting solid was filtered, washed with acetone and the filtrate was concentrated under reduced pressure. The crude residue was purified by silica gel chromatography (0-30% EtOAc/Hexanes gradient) to afford 1.6 g of the desired product as an off-white solid: LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, Retention Time=3.81 minutes (M+H) 378.06.

후처리

  1. filtrationThe resulting solid was filtered
  2. washwashed with acetone
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe crude residue was purified by silica gel chromatography (0-30% EtOAc/Hexanes gradient)

출처 및 근거

ORD 기록
ord-84b2667bf713490fba43efd373d0ca9e
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394302B2

반응 노트

불러오는 중…